Juvabione and its analogues. II. Isolation, identification, and occurrence of juvabiol and its epimer isojuvabiol from the whole wood of Abies balsamea

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Abstract
Epimeric mixtures of juvabiol (3a) and isojuvabiol (4a) have been detected in six North American Abies balsamea (L.) Mill. trees and isolated from the whole-wood extract of three. These juvabione related alcohols are insect juvenile hormone analogues with selective action typical of juvabione (1) and Δ4′-dehydrojuvabione (2). The widespread occurrence of these alcohols indicates that the original 'paper factor' was not due to 1 alone, nor was it due to a mixture of 1 and 2. In addition a fifth IJHA with selective action, Δ3′-dehydrojuvabi-5′-ol (5), was detected in the hot ethanol extract of four trees and isolated from one tree. It is shown that 5 is an allylic rearrangement product of the Δ4′-dehydrojuvabiols 6a and 7a. Mixtures of campesterol and sitosterol are the major crystalline components present in all the petroleum ether soluble extracts.

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